When babies are first born they’re like little dolls…at least insofar as they have no opinion on what they wear or how we dress them. We can spend as little or much time (and money) on their attire as we’d like, and for those of us who like fashion this can be such a fun aspect of becoming a parent. 

Until my boys were probably 5 years old, they didn’t care at all what they wore, and I felt very lucky for that. Not only did we avoid battles over the comfort of their clothing or the inclusion of their favorite characters on every t-shirt, backpack or dress, but I got to define their style from their sports clothes to their “dressier” outfits and their school accessories. 

Once kindergarten hit, they each began to have opinions of their own, and (begrudgingly) I knew I had to give them the independence to begin making their own choices and getting themselves dressed every day. I wasn’t ready to entirely relinquish control and have my kids looking like a hot mess, but I think there’s a balance between teaching kids how to dress presentably and giving them the freedom to express themselves. 

Skirt - Jacket - Boots - Kibou 

Teaching Kids How to Dress Themselves:

Even in elementary school, I think the way we present ourselves has a subconscious impact on how others perceive us…I’m also aware that this might just be a shallow worry that my children are a reflection of me, and that I care too much what others think. (Note to self: as they grow, I definitely have to learn to let go of that idea.)

Rather than just leave it up to chance that they should find two pieces of clothing that go together, I wanted to find a way to teach my boys how to think about style. 

1. Give choices starting early: Starting around 2½  I would set out a couple of outfits for my kids to choose between. This way they had a sense of agency when they were already looking for control in everything in their life, and they could begin to see what clothes go together, even if only subconsciously.
   
   
2. Highlight why the clothes go together: Continuing to give them choices, around 3 or 4 years old, I started to point out why I put certain shorts and shirts together. For example: this gray Nike t-shirt goes with these navy blue mesh shorts, because they’re both sports clothes. And then I’d ask why is this the right kind of clothing for camp today? 
   
   I recently read a suggestion I loved: decorate or dress paper dolls with your kids as a way of incorporating fashion and style into play–making it easier to discuss why things match or what styles look good together. I haven’t tried this with my boys, but I can imagine them having fun with it!.
   
   
3. Organize drawers by category: Like in the example above, I think it’s easiest to help kids understand that certain types of clothing go together and others don’t, for example, generally you wear a sweater with jeans or nicer pants, not usually with athletic pants. If you need something warm to wear with casual shorts, sweatshirts make more sense. To help make it easier to choose which shirts go with which bottoms, I organize their shirts into 4 categories and their pants/shorts into 4: casual/sports, dressier, long and short. Girls’ clothes admittedly require a few extra categories including skirts and leggings.
   
   
4. Discuss special occasions:Helping my kids understand why we dress differently for special occasions has definitely helped to reduce the debate that can ensue before getting dressed for holidays or fancier occasions. I try to keep it simple; dressing up gives everyone–ourselves and the people we’re with–a sense of the day being more special. Just like we wear a team uniform for sports or bathing suits to the beach, there are certain clothes that are right for dinner at a nice restaurant or a Broadway show. 
   
   
5. Recognize comfort always matters: period. From the waistband of their undies to the material and tags of their clothes, looking good should never come at the expense of comfort.

T-shirt - Pants - Beanie - Kibou 

A Few Ground Rules

Aside from trying to teach them about fashion, I do have a few rules to maintain clear expectations:

1. Weather dictates attire, and parents have final say. If it’s 48 degrees outside, you must wear pants, but you can pick which ones.
2. Certain occasions require certain types of clothing. If we’re going to a Broadway show, you can’t wear athletic shorts or sweatpants. I’ll give you a few options and you can take your pick.
3. They can/should veto anything they don’t like and won’t wear when we go shopping (or if I buy online, they can choose what to return). This gives them a sense of agency…and keeps me from wasting money on wishful thinking that they’ll ever actually wear the corduroys. 
4. If they want a certain character on their clothing, assuming they are age-appropriate, I’ll find options to choose from. I try to avoid more than a couple of these in their wardrobe.

In Conclusion…

As with parenting, providing guardrails around what they do (or in this case, what they can choose to wear) can help maintain a certain level of order. They are more likely to put together outfits that match if I minimize the broad spectrum of colors and patterns in their wardrobe. Personally, I tend to go with neutrals throughout the year and introduce more fun colors or patterns in the warm weather months.

And in support of their independence beyond just what they choose to wear, I include them in the shopping process by putting together an online shopping cart from which they can pick out what they like (this goes for sneakers, clothes, and accessories). 

Ultimately, kids’ style choices and ability to dress themselves is a bit of a microcosm of parenting and childhood overall: it’s about giving them some knowledge, scaffolding choices and leaving space for independence. As a parent it’s an exercise in letting go. At the end of the day, it’s just clothes, and sometimes it’s not a battle worth having. As long as what they are wearing is seasonally appropriate (and at least relatively appropriate for the occasion, given the child’s age) it’s okay for kids to look ridiculous sometimes. Their body and clothes are their own and it’s important to give them independence in this way, just like it is with other aspects of their lives.